Hexafluoroisopropanol-Promoted Disulfidation and Diselenation of Alkyne, Alkene, and Allene

Article abstract of DOI:10.1021/acs.orglett.0c01834

Hexafluoroisopropanol (HFIP)-promoted disulfidation and diselenation of C-C unsaturated bonds is reported. Reactions of unactivated alkyne, alkene, and allene, respectively, with disulfides or diselenides in HFIP led to desired products in good to excellent yields (up to 96percent). In contrast, other solvents, such as isopropanol and dichloroethane, could not promote the same reaction. This method revealed an example of HFIP-promoted transformations under the mild conditions, which greatly highlighted the unique reactivity of this special solvent.

Full text of DOI:10.1021/acs.orglett.0c01834

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Letter
Hexafluoroisopropanol-Promoted Disulfidation and Diselenation of
Alkyne, Alkene, and Allene
Chiyu Wei, Ying He, Jin Wang, Xiaohan Ye, Lukasz Wojtas, and Xiaodong Shi*
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ABSTRACT: Hexafluoroisopropanol (HFIP)-promoted disulfidation and diselenation of C−C unsaturated bonds is reported.
Reactions of unactivated alkyne, alkene, and allene, respectively, with disulfides or diselenides in HFIP led to desired products in
good to excellent yields (up to 96%). In contrast, other solvents, such as isopropanol and dichloroethane, could not promote the
same reaction. This method revealed an example of HFIP-promoted transformations under the mild conditions, which greatly
highlighted the unique reactivity of this special solvent.
Scheme 1. HFIP-Promoted Challenging Transformations
ne basic mission of synthetic chemistry is to develop new
Omethods for effective transformations, achieving a
complex molecular scaffold from simple starting materials
under mild conditions.1 As one of the crucial reaction tuning
factors, solvent could dramatically impact the reaction
performance. With the discovery of ionic liquid and fluorinated
solvents, unexpected results were obtained, greatly enriching
the synthetic toolbox.2 Fluorinated compounds have received
tremendous attention in chemical, medicinal, and material
research.3 The high electronegativity and good hydrophobicity
of the fluorine atom give fluorinated compounds unique
chemical properties. Recently, HFIP has emerged as a unique
polar organic solvent in promoting chemical reactions.4 With
two acidic protons, low nucleophilicity, and high ionizing
power, HFIP has been used as an alternative solvent in
substituting Lewis acid or Brønsted acid in promoting chemical
transformations through H-bond networks under very mild
conditions. In addition, HFIP is a promising solvent in
industrial processing, owing to its recyclability and low cost.5
Some representative HFIP-promoted transformations, includ-
ing the Friedel−Crafts reaction,6 polyene cyclization,7 and
Schmidt reaction,8 are shown in Scheme 1A. In comparison
with other solvents which failed to produce the desired
products, HFIP significantly promoted the reaction to obtain
good to excellent yields. These results greatly highlighted the
unique reactivity of HFIP in facilitating organic trans-
formations under mild conditions.
solvent effect of HFIP on diselenation and disulfidation of the
C−C unsaturated bond. Good to excellent yields were
Received: May 31, 2020
Recently, we reported thioallylation and diselenation of
alkynes under gold redox catalysis.9 Based on the solvent
screening, we observed that HFIP could greatly promote the
reaction of even more challenging unactivated internal alkyne
without gold catalysts. Herein, we report this interesting
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A

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achieved with broad reaction substrate scope under metal-free
conditions (Scheme 1B), which demonstrated the unique
reactivity of the HFIP solvent in promoting challenging
organic transformations.
these results, we evaluated the reaction scope of this metal-free
HFIP promoted transformations. The results are summarized
in Scheme 2.
Disulfidation10 and diselenation11 of C−C unsaturated
bonds are the basic organic transformations with many
chemical and medicinal applications. Great progress has been
made regarding these transformations by using transition metal
promoters/catalysts, Lewis acid, and photocatalysts to achieve
the desired products. Our interest in this reaction was
originated from our continuous efforts in gold-catalyzed alkyne
activation.12 As shown in Figure 1A, we recently reported the
a
Scheme 2. HFIP-Promoted Alkyne Diselenation
a
Reaction conditions: alkyne (0.4 mmol) and diselenide (0.2 mmol)
were added into HFIP/HFA = 19:1 (1 mL), and the mixture was
b
c
stirred at 60 °C for 24 h. Isolated yield. 3 days. Under room
d
temperature. 12 h.
Figure 1. HFIP-promoted internal alkyne diselenation.
diselenation of alkynes through a gold(I)−gold(III) redox
catalytic cycle, giving diselenation products in excellent yields
with high stereoselectivity (trans-addition only). However, this
transformation did not work well on simple internal alkynes,
even with an increased catalyst loading (10% [Au]) at 60 °C.
As shown in Figure 1B, treating internal alkyne 1a with
diselenide 2a under previous gold catalytic conditions (DCE,
60 °C, 24 h) gave diselenation product 3a in poor conversion
(15%) and low yield (14%) associated with completed gold
catalyst decomposition. Interestingly, switching the solvent to
HFIP greatly enhanced the reaction performance, giving 3a in
nearly quantitative yield (93%). A control reaction using HFIP
as solvent without gold catalyst was then carried out, achieving
3a in 78% yield with 80% conversion of 1a in 24 h. Extending
the reaction time to 36 h gave a full conversion of 1a, and the
desired product 3a was obtained in excellent yield (95%).
HFIP is necessary to be a solvent (0.2 M). When applying a
mixture of DCE/HFIP (9:1), only trace amount of product
was obtained. In addition, applying hexafluoroacetone (HFA)
as additive could accelerate the reaction with comparable yield
in 30 h (for detailed screening of the optimal ratio of HFIP/
HFA, see Table S1). Other solvents, including iPrOH, DMSO,
DMF, CH3CN, acetone, chlorobenzene, and nitromethane,
could not promote this reaction, resulting in less than 5% yield
in all cases. Lowering the temperature to 40 °C led to a
decrease of conversion due to slower reaction kinetics. The
detailed screening conditions are summarized in the
Supporting Information. Notably, only trans-isomer 3a was
observed under these metal-free conditions, suggesting a
concerted bimolecular trans-addition of diselenides to the
plausible selenium cation intermediate formed from alkyne
addition toward HFIP-activated diselenides. Encouraged by
Various substituted alkynes were evaluated in this HFIP
“boosted” transformation. First, several diaryl acetylenes with
different substituents on the aromatic rings were tested. Both
electron-donating group (EDG) and electron-withdrawing
group (EWG) substituted aromatic rings worked well in this
reaction, giving the desired products (3a−3h) in excellent
yields. Second, aliphatic alkynes (3i−3q) gave similar results
with the desired products obtained mostly in excellent yields.
The cyclopropyl-substituted alkyne (3q) gave no ring-opening
product, ruling out the potential radical mechanism. Third, a
series of diselenides were also employed for this transformation
(3r−3v), giving the expected products in good to excellent
yields. A lower yield was observed with dibenzylselenide 3w
due to the slow reaction rate. The terminal alkynes (3x, 3y)
did not work under these HFIP conditions. After switching the
conditions to Au catalysis, significantly improved yields were
obtained. Notably, when HFIP was used as solvent instead of
DCE, the reaction performance could be improved to 93% and
80%, respectively. No racemization of the chiral center on the
amino acid after reaction highlighted the mild conditions as
well as the great promoting effects of HFIP solvent in gold
redox catalysis (for chiral HPLC characterization, see section
VI in the Supporting Information).
Although the detailed mechanism of this HFIP-promoting
effect remains to be explored, one plausible reason behind this
“boosting effect” is that HFIP activates RSeSeR to form a
selenium species as a good leaving group through an H-bond
network.4j Therefore, under a gold catalytic pathway, this
HFIP boosting effect could help the oxidation of gold(I) to
gold(III)with the activated selenium, which is likely the
turnover-limiting step. Similarly, in the nonmetal catalytic
conditions, diselenides are good electrophiles that form an
B
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equilibrium with alkyne addition. This hypothesis also
explained the reason why carbonyl-conjugated alkynes (3x,
3y), as bad nucleophiles, did not work under nonmetal
catalytic conditions. The cation-stabilizing effect of HFIP
would also help the activation of unsaturated substrates under
HFIP/Au conditions.5 Overall, through the formation of H-
bond, HFIP could greatly assist diselenides activation and
increase the reactivity of this diselenation. Based on this
hypothesis, we wondered if this activation mode could be
applied to similar transformations using alkene and allene as
the substrate. To confirm this idea, reactions of diselenides
with alkenes and allenes were performed.
for aliphatic alkynes, see Table S3). Overall, this result greatly
highlighted the boosting effect of HFIP solvent applied in gold
catalysis, which was critical for alkyne activations.
Furthermore, reactions of disulfide with alkene under the
HFIP conditions gave the desired product 6a in 91% yield with
gram-scale synthesis. Some representative alkenes were tested
with the desired disulfidation products obtained in good to
excellent yields (6b−6e). Notably, the 1,2-disubstituted
alkene, cis-stilbene, accomplished the reaction in excellent
yield (6e, 93%), while the trans-stilbene did not work under
these conditions. Notably, other solvents, such isopropanol
and DCE, gave almost no reaction (<5%). Allene was also
tested under the HFIP conditions, with or without gold
catalyst presented. Moderate yield was observed using
nonmetal conditions. With gold catalyst present, no signifi-
cantly improved yield was observed in HFIP compared with
DCE solvents due to the decomposition of product in HFIP.
Nevertheless, HFIP presented a solvent-promoting effect over
other solvents, suggesting this boosting effect could also be
applied in C−C unsaturated bonds in the disulfidation reaction
under mild conditions.
As shown in Figure 2A, styrene failed to give the
diselenation product with the formation of complex reaction
In conclusion, the diselenation and disulfidation of C−C
unsaturated bonds were reported using HFIP as the promoting
solvent. Compared with other common organic solvents, HFIP
greatly enhanced the reaction performance by activating the
diselenide and disulfide through H-bond networks. The
desired products were achieved under mild conditions with
good to excellent yield and high stereoselectivity. These results
offered another prospective use of HFIP as the solvent to boost
the reactivity of substrates and achieve challenging trans-
formations.
ASSOCIATED CONTENT
■
sı
* Supporting Information
The Supporting Information is available free of charge at
https://pubs.acs.org/doi/10.1021/acs.orglett.0c01834.
Experimental details, NMR spectra, and details of the
experiments (PDF)
Accession Codes
Figure 2. Disulfidation and diselenation reactions.
CCDC 2006688−2006689 contain the supplementary crys-
tallographic data for this paper. These data can be obtained
free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by
emailing data_request@ccdc.cam.ac.uk, or by contacting The
Cambridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
mixtures without diselenation product. With allene substrates,
lower yields were observed. Monitoring the reactions with
NMR revealed the decomposition of products over time under
the reaction conditions. The addition of gold catalyst in the
allene case could give a faster reaction. As a result, improved
yields were observed (Figure 2A).
Considering that HFIP might provide a similar H-bond
activation effect toward disulfide (RSSR), we started out our
investigations on disulfidation with various unsaturated C−C
bonds under Au/HFIP conditions. For alkyne substrates
(Figure 2B), HFIP could not promote this transformation,
giving the desired disulfide products in low yield. In
comparison, the combination of gold and HFIP afforded the
desired products in good yield (72%), while DCE solvent gave
only a trace amount of product. Different internal and terminal
alkynes were tested with desired products observed in good to
excellent yields (5a−5e). Aliphatic substituted alkynes, both
internal and terminal, give almost no products under either
HFIP or HFIP/Au catalysis conditions (for the detailed scope
AUTHOR INFORMATION
■
Corresponding Author
Xiaodong Shi − Department of Chemistry, University of South
Florida, Tampa, Florida 33620, United States; orcid.org/
0000-0002-3189-1315; Email: xmshi@usf.edu
Authors
Chiyu Wei − Department of Chemistry, University of South
Florida, Tampa, Florida 33620, United States
Ying He − Department of Chemistry, University of South
Florida, Tampa, Florida 33620, United States
Jin Wang − College of Chemistry, Chemical Engineering and
Material Science, Shandong Normal University, Jinan,
Shandong 250014, China
C
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Xiaohan Ye − Department of Chemistry, University of South
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Lukasz Wojtas − Department of Chemistry, University of South
Florida, Tampa, Florida 33620, United States
Complete contact information is available at:
https://pubs.acs.org/10.1021/acs.orglett.0c01834
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The authors declare no competing financial interest.
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ACKNOWLEDGMENTS
We are grateful to the NSF (CHE-1665122) and NIH
(1R01GM120240-01) for financial support.
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